Co(III)-salen catalyzed carbenoid reaction: Stereoselective [2,3]sigmatropic rearrangement of S-ylides derived from allyl aryl sulfides

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3435-3438

  Fukuda, Tsutomu ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031006727     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00639-4     Document Type: Article

References (18)

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9. c) Kokubo, C.; Katsuki, T. Tetrahedron 1996, 52, 13895-13900.
10. a) Fukuda, T.; Katsuki, T. Synlett 1995, 825-826.
11. b) Fukuda, T.; Katsuki, T. Tetrahedron in press.
12. Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
13. Co-salen catalysts bearing substituents at 3-and 3′-carbons showed very poor catalytic activity for S-ylide formation reaction, as expected.
14. This means that % ees of major and minor isomers should be equal. Actually, both the isomers obtained with 4 and tert-butyl diazoacetate showed the same enantioselectivity of 64% ee (Table 1, entry 4).
15. Ito, K.; Yoshitake, M.; Katsuki, T. Heterocycles 1996, 42, 305-317.
16. 3). The diastereomers could not be separated.
17. Configuration of the major diastereomer was tentatively assigned to be anti by the mechanical analogy with [2,3]sigmatropic rearrangement of the S-ylide derived from cinnamyl phenyl sulfide.
18. 2 and the corresponding Schiff base which was in turn prepared from 2-hydroxy-5-methoxybenzaldehyde and (1R,2R)-1,2-diphenylethylenediamine.